Controlling the physical and biological properties of highly fluorescent aqueous quantum dots using block copolymers of different size and shape

ACS Nano

Volumn 7, Issue 10, 2013, Pages 9156-9167

  Ostermann, Johannes ^a   Merkl, Jan Philip ^a   Flessau, Sandra ^a   Wolter, Christopher ^a   Kornowksi, Andreas ^a   Schmidtke, Christian ^a   Pietsch, Andrea ^a   Kloust, Hauke ^a   Feld, Artur ^a   Weller, Horst ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

amphiphilic diblock copolymer; cellular uptake; copper mediated click reaction; fluorescence quenching; micelles; phase transfer; quantum dots

Indexed keywords

AMPHIPHILIC DIBLOCK COPOLYMERS; CELLULAR UPTAKE; CLICK REACTION; FLUORESCENCE QUENCHING; PHASE TRANSFER;

COPPER; FLUORESCENCE; MICELLES; NANOPARTICLES; POLYMERS; QUENCHING; SEMICONDUCTOR QUANTUM DOTS; SHELLS (STRUCTURES);

BLOCK COPOLYMERS;

POLYMER; QUANTUM DOT; WATER;

ANIMAL; ARTICLE; CELL LINE; CHEMISTRY; FLUORESCENCE; HUMAN; MOUSE; TRANSMISSION ELECTRON MICROSCOPY;

ANIMALS; CELL LINE; FLUORESCENCE; HUMANS; MICE; MICROSCOPY, ELECTRON, TRANSMISSION; POLYMERS; QUANTUM DOTS; WATER;

EID: 84886998778     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn4037859     Document Type: Article

References (53)

1. Medintz, I. L.; Uyeda, H. T.; Goldman, E. R.; Mattoussi, H. Quantum Dot Bioconjugates for Imaging, Labelling and Sensing Nat. Mater. 2005, 4, 435-446
2. Chen, O.; Zhao, J.; Chauhan, V. P.; Cui, J.; Wong, C.; Harris, D. K.; Wei, H.; Han, H.-S.; Fukumura, D.; Jain, R. K. et al. Compact High-Quality CdSe-CdS Core-Shell Nanocrystals with Narrow Emission Linewidths and Suppressed Blinking Nat. Mater. 2013, 12, 1-7
3. Resch-Genger, U.; Grabolle, M.; Cavaliere-Jaricot, S.; Nitschke, R.; Nann, T. Quantum Dots versus Organic Dyes as Fluorescent Labels Nat. Methods 2008, 5, 763-775
4. Mekis, I.; Talapin, D. V.; Kornowski, A.; Haase, M.; Weller, H. One-Pot Synthesis of Highly Luminescent CdSe/CdS Core-Shell Nanocrystals via Organometallic and "Greener" Chemical Approaches J. Phys. Chem. B 2003, 107, 7454-7462
5. Thiry, M.; Boldt, K.; Nikolic, M. S.; Schulz, F.; Ijeh, M.; Panicker, A.; Vossmeyer, T.; Weller, H. Fluorescence Properties of Hydrophilic Semiconductor Nanoparticles with Tridentate Polyethylene Oxide Ligands ACS Nano 2011, 5, 4965-4973
6. Uyeda, H. T.; Medintz, I. L.; Jaiswal, J. K.; Simon, S. M.; Mattoussi, H. Synthesis of Compact Multidentate Ligands to Prepare Stable Hydrophilic Quantum Dot Fluorophores J. Am. Chem. Soc. 2005, 127, 3870-3878
7. Pellegrino, T.; Manna, L.; Kudera, S.; Liedl, T.; Koktysh, D.; Rogach, A. L.; Keller, S.; Ra, J.; Natile, G.; Parak, W. J. Hydrophobic Nanocrystals Coated with an Amphiphilic Polymer Shell: A General Route to Water Soluble Nanocrystals Nano Lett. 2004, 4, 703-707
8. Pöselt, E.; Fischer, S.; Foerster, S.; Weller, H. Highly Stable Biocompatible Inorganic Nanoparticles by Self-Assembly of Triblock-Copolymer Ligands Langmuir 2009, 25, 13906-13913
9. Chan, Y.; Zimmer, J. P.; Stroh, M.; Steckel, J. S.; Jain, R. K.; Bawendi, M. G. Incorporation of Luminescent Nanocrystals into Monodisperse Core-Shell Silica Microspheres Adv. Mater. 2004, 16, 2092-2097
10. Kloust, H.; Pöselt, E.; Kappen, S.; Schmidtke, C.; Kornowski, A.; Pauer, W.; Moritz, H.-U.; Weller, H. Ultrasmall Biocompatible Nanocomposites: a New Approach Using Seeded Emulsion Polymerization for the Encapsulation of Nanocrystals Langmuir 2012, 28, 7276-7281
11. Rostovtsev, V. V; Green, L. G.; Fokin, V. V; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599
12. Brennan, J. L.; Hatzakis, N. S.; Tshikhudo, T. R.; Dirvianskyte, N.; Razumas, V.; Patkar, S.; Vind, J.; Svendsen, A.; Nolte, R. J. M.; Rowan, A. E. et al. Bionanoconjugation via Click Chemistry: The Creation of Functional Hybrids of Lipases and Gold Nanoparticles Bioconjugate Chem. 2006, 17, 1373-1375
13. Boisselier, E.; Salmon, L.; Ruiz, J.; Astruc, D. How to Very Efficiently Functionalize Gold Nanoparticles by "Click" Chemistry Chem. Commun. 2008, 5788-5790
14. Binder, W. H.; Sachsenhofer, R.; Straif, C. J.; Zirbs, R. Surface-Modified Nanoparticles via Thermal and Cu(I)-Mediated "Click" Chemistry: Generation of Luminescent CdSe Nanoparticles with Polar Ligands Guiding Supramolecular Recognition J. Mater. Chem. 2007, 17, 2125-2132
15. Beaune, G.; Tamang, S.; Bernardin, A.; Bayle-Guillemaud, P.; Fenel, D.; Schoehn, G.; Vinet, F.; Reiss, P.; Texier, I. Luminescence of Polyethylene Glycol Coated CdSeTe/ZnS and InP/ZnS Nanoparticles in the Presence of Copper Cations ChemPhysChem 2011, 12, 2247-2254
16. Isarov, A. V.; Chrysochoos, J. Optical and Photochemical Properties of Nonstoichiometric Cadmium Sulfide Nanoparticles: Surface Modification with Copper(II) Ions Langmuir 1997, 13, 3142-3149
17. 4 Quantum Dots ACS Nano 2013, 7, 3190-3197
18. Chen, D.; Viswanatha, R.; Ong, G. L.; Xie, R.; Balasubramaninan, M.; Peng, X. Temperature Dependence of "Elementary Processes" in Doping Semiconductor Nanocrystals J. Am. Chem. Soc. 2009, 131, 9333-9339
19. Srivastava, B. B.; Jana, S.; Pradhan, N. Doping Cu in Semiconductor Nanocrystals: Some Old and Some New Physical Insights J. Am. Chem. Soc. 2011, 133, 1007-1015
20. Bernardin, A.; Cazet, A.; Guyon, L.; Delannoy, P.; Vinet, F.; Bonnaffé, D.; Texier, I. Copper-Free Click Chemistry for Highly Luminescent Quantum Dot Conjugates: Application to in Vivo Metabolic Imaging Bioconjugate Chem. 2010, 21, 583-588
21. Schieber, C.; Bestetti, A.; Lim, J. P.; Ryan, A. D.; Nguyen, T.-L.; Eldridge, R.; White, A. R.; Gleeson, P. a; Donnelly, P. S.; Williams, S. J. et al. Conjugation of Transferrin to Azide-Modified CdSe/ZnS Core-Shell Quantum Dots Using Cyclooctyne Click Chemistry Angew. Chem., Int. Ed. 2012, 51, 10523-10527
22. Zhang, P.; Liu, S.; Gao, D.; Hu, D.; Gong, P.; Sheng, Z.; Deng, J.; Ma, Y.; Cai, L. Click-Functionalized Compact Quantum Dots Protected by Multidentate-Imidazole Ligands: Conjugation-Ready Nanotags for Living-Virus Labeling and Imaging J. Am. Chem. Soc. 2012, 134, 8388-8391
23. Breus, V. V.; Heyes, C. D.; Nienhaus, G. U. Quenching of CdSe-ZnS Core-Shell Quantum Dot Luminescence by Water-Soluble Thiolated Ligands J. Phys. Chem. C 2007, 111, 18589-18594
24. 2S Nanorods with Tunable Composition Probed by Ultrafast Transient Absorption Spectroscopy J. Phys. Chem. B 2010, 114, 5879-5885
25. Boldt, K.; Jander, S.; Hoppe, K.; Weller, H. Characterization of the Organic Ligand Shell of Semiconductor Quantum Dots by Fluorescence Quenching Experiments ACS Nano 2011, 5, 8115-8123
26. Ji, X.; Palui, G.; Avellini, T.; Na, H. B.; Yi, C.; Knappenberger, K. L.; Mattoussi, H. On the pH-Dependent Quenching of Quantum Dot Photoluminescence by Redox Active Dopamine J. Am. Chem. Soc. 2012, 134, 6006-6017
27. Pons, T.; Medintz, I. L.; Sapsford, K. E.; Higashiya, S.; Grimes, A. F.; English, D. S.; Mattoussi, H. On the Quenching of Semiconductor Quantum Dot Photoluminescence by Proximal Gold Nanoparticles Nano Lett. 2007, 7, 3157-3164
28. Pöselt, E.; Schmidtke, C.; Fischer, S.; Peldschus, K.; Salamon, J.; Kloust, H.; Tran, H.; Pietsch, A.; Heine, M.; Adam, G. et al. Tailor-Made Quantum Dot and Iron Oxide Based Contrast Agents for in Vitro and in Vivo Tumor Imaging ACS Nano 2012, 6, 3346-3355
29. Schmidtke, C.; Pöselt, E.; Ostermann, J.; Pietsch, A.; Kloust, H.; Tran, H.; Schotten, T.; Bastús, N. G.; Eggers, R.; Weller, H. Amphiphilic, Cross-Linkable Diblock Copolymers for Multifunctionalized Nanoparticles as Biological Probes Nanoscale 2013, 5, 7433-7444
30. 4 Macromolecules 1999, 32, 2783-2785
31. Allgaier, J.; Poppe, A.; Willner, L.; Richter, D. Synthesis and Characterization of Poly[1,4-isoprene-b-(ethylene oxide)] and Poly[ethylene-co-propylene-b-(ethylene oxide)] Block Copolymers Macromolecules 1997, 30, 1582-1586
32. Al-Jarrah, M. M. F.; Apikian, R. L.; Ahmed, E. Polymerization Mechanisms Polym. Bull. 1984, 12, 433-436
33. Schmidtke, C.; Lange, H.; Tran, H.; Ostermann, J.; Kloust, H.; Bastús, N. G.; Merkl, J.-P.; Thomasen, C.; Weller, H. Radical Initiated Reactions on Biocompatible CdSe-Based Quantum Dots: Ligand Crosslinking, Crystal Annealing and Fluorescence Enhancement J. Phys. Chem. C 2013, 117, 8570-8578
34. Zalipsky, S. Functionalized Poly(ethylene glycol) for Preparation of Biologically Relevant Conjugates Bioconjugate Chem. 1995, 6, 150-165
35. 2-Miktoarm Stars Macromolecules 2011, 44, 9887-9890
36. 2B Miktoarm Stars vs AB Diblocks Macromolecules 2000, 33, 1741-1746
37. Cai, Y.; Tang, Y.; Armes, S. P. Direct Synthesis and Stimulus-Responsive Micellization of Y-Shaped Hydrophilic Block Copolymers Macromolecules 2004, 37, 9728-9737
38. 2B Miktoarm Star Polymers Biomaterials 2010, 31, 8382-8392
39. Gibanel, S.; Forcada, J.; Heroguez, V.; Schappacher, M.; Gnanou, Y. Novel Gemini-Type Reactive Dispersants Based on PS/PEO Block Copolymers: Synthesis and Application Macromolecules 2001, 34, 4451-4458
40. 2B Y-Shaped Miktoarm Star Copolymers of ε-Caprolactone and 2-(Dimethylamino)ethyl Methacrylate J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 1446-1462
41. Gao, Z.; Eisenberg, A. A Model of Micellization for Block Copolymers in Solutions Macromolecules 1993, 26, 7353-7360
42. Wilhelm, M.; Zhao, C.; Wang, Y.; Xu, R.; Winnik, M. A.; Mura, J.-L.; Riess, G.; Croucher, M. D. Poly(styrene-ethylene Oxide) Block Copolymer Micelle Formation in Water: a Fluorescence Probe Study Macromolecules 1991, 24, 1033-1040
43. Kangwansupamonkon, W.; Gilbert, R. G.; Kiatkamjornwong, S. Modification of Natural Rubber by Grafting with Hydrophilic Vinyl Monomers Macromol. Chem. Phys. 2005, 206, 2450-2460
44. Hühn, D.; Kantner, K.; Geidel, C.; Brandholt, S.; Cock, I. De; Soenen, S. J. H.; Rivera Gil, P.; Montenegro, J.-M.; Braeckmans, K.; Müllen, K. et al. Polymer-Coated Nanoparticles Interacting with Proteins and Cells: Focusing on the Sign of the Net Charge ACS Nano 2013, 7, 3253-3263
45. Mahmoudi, M.; Abdelmonem, A. M.; Behzadi, S.; Clement, J. H.; Dutz, S.; Ejtehadi, M. R.; Hartmann, R.; Kantner, K.; Linne, U.; Maffre, P. et al. Temperature-The "Ignored" Factor at the NanoBio Interface ACS Nano 2013, 10.1021/nn305337c
46. Lakowicz, J. Principles of Fluorescence Spectroscopy; 3 rd ed.; Springer: New York, 2010.
47. Beaune, G.; Tamang, S.; Bernardin, A.; Bayle-Guillemaud, P.; Fenel, D.; Schoehn, G.; Vinet, F.; Reiss, P.; Texier, I. Luminescence of Polyethylene Glycol Coated CdSeTe/ZnS and InP/ZnS Nanoparticles in the Presence of Copper Cations ChemPhysChem 2011, 12, 2247-2254
48. Chen, Y.; Rosenzweig, Z. Luminescent CdS Quantum Dots as Selective Ion Probes Anal. Chem. 2002, 74, 5132-5138
49. Kriegel, I.; Jiang, C.; Rodríguez-Fernández, J.; Schaller, R. D.; Talapin, D. V; Como, E. da; Feldmann, J. Tuning the Excitonic and Plasmonic Properties of Copper Chalcogenide Nanocrystals J. Am. Chem. Soc. 2012, 134, 1583-1590
50. Hassane, F. S.; Frisch, B.; Schuber, F. Targeted Liposomes: Convenient Coupling of Ligands to Preformed Vesicles Using "Click Chemistry. Bioconjugate Chem. 2006, 17, 849-854
51. Winstein, S.; Goodman, L. Neighboring Groups in Addition. II. Hydroxyl and Acetoxy Groups in Allyl Derivatives J. Am. Chem. Soc. 1954, 76, 4368-4372
52. Marasco, C. J.; Piantadosi, C.; Meyer, K. L.; Morris-Natschke, S.; Ishaq, K. S.; Small, G. W.; Daniel, L. W. Synthesis and Biological Activity of Novel Quaternary Ammonium Derivatives of Alkylglycerols as Potent Inhibitors of Protein Kinase C J. Med. Chem. 1990, 33, 985-992
53. Talapin, D. V.; Mekis, I.; Götzinger, S.; Kornowski, A.; Benson, O.; Weller, H. CdSe/CdS/ZnS and CdSe/ZnSe/ZnS Core-Shell-Shell Nanocrystals J. Phys. Chem. B 2004, 108, 18826-18831